8-fluoro and 7,8,10-trifluoro-9-(substituted)-6-oxo-6H-benzo(C)quinolizine-5-carboxylic acids

Abstract

Novel substituted quinolinecarboxylic acid derivatives of the formula: ##STR1## wherein R 1 is hydrogen, alkali metal, alkaline earth metal or lower alkyl; R 2 is hydrogen, benzyl or alkyl(C 1 -C 3 ); X is hydrogen or fluoro; which have antibacterial activity, intermediates useful in the preparation of the compounds, methods of producing and using the compounds to treat bacterial infections in animals.

What is claimed is: 
     
       1. A compound of the formula: ##STR6## wherein R 1  is hydrogen, alkyl(C 1  -C 3 ), alkali metal, or alkaline earth metal; R 2  is hydrogen, benzyl or alkyl(C 1  -C 3 ); X is hydrogen or fluoro; and when R 1  is hydrogen, a pharmaceutically acceptable salt thereof. 
     
     
       2. A compound according to claim 1, which is selected from the group consisting of ethyl 8-fluoro-9-(4-methyl-1-piperazinyl)-6-oxo-6H-benzo[c]quinolinine5-carboxylate; 8-fluoro-9-(4-methyl-1-piperazinyl)-6-oxo-6H-benzo[c]quinolizine-5-carboxylic acid; ethyl 8-fluoro-9(1-piperazinyl)-6-oxo-6H-benzo[c]quinolizine-5-carboxylate; 8-fluoro-9-(1-piperazinyl)-6-oxo-6H-benzo[c]quinolizine-5-carboxylic acid; ethyl 7,8,10-trifluoro-9-(4-methyl-1-piperazinyl)-6-oxo-6H-benzo[c]quinolizine-5-carboxylate; 7,8,10-trifluoro-9-(4-methyl-1-piperazinyl)-6-oxo-6H-benzo[c]quinolizine-5-carboxylic acid; ethyl 7,8,10-trifluoro-9-(1-piperazinyl)-6-oxo-6H-benzo[c]quinolizine-5-carboxylate; and 7,8,10-trifluoro-9-(1-piperazinyl)-6-oxo-6H-benzo[c]quinolizine-5-carboxylic acid. 
     
     
       3. A method of treating bacterial infections in warm-blooded animals which comprises administering to said animals an antibacterially effective amount of a compound selected from those of claim 1. 
     
     
       4. A pharmaceutical composition for treating bacterial infections in dosage unit form comprising from 100 to 750 mg of a compound selected from those of claim 1 in association with a pharmaceutically acceptable carrier.